Concise Synthesis of Broussonone A
A concise and expeditious approach to the total synthesis of broussonone A, a p-quinol natural compound, has been developed. The key features of the synthesis include the Grubbs II catalyst mediated cross metathesis of two aromatic subunits, and a chemoselective oxidative dearomatizationin the pres...
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| Language: | English |
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MDPI AG
2015-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/9/15966 |
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doaj-e5c9ac6f62f3421cab71a99625cb423d2020-11-24T21:17:55ZengMDPI AGMolecules1420-30492015-09-01209159661597510.3390/molecules200915966molecules200915966Concise Synthesis of Broussonone AHyeju Jo0Minho Choi1Mayavan Viji2Young Hee Lee3Young-Shin Kwak4Kiho Lee5Nam Song Choi6Yeon-Ju Lee7Heesoon Lee8Jin Tae Hong9Mi Kyeong Lee10Jae-Kyung Jung11College of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy, Korea University, Sejong 339-700, KoreaCollege of Pharmacy, Korea University, Sejong 339-700, KoreaCollege of Interdisciplinary & Creative Studies, Konyang University, Nonsan 320-711, KoreaKorea Ocean Research and Development Institute, Ansan 426-44, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaCollege of Pharmacy and Medicinal Research Center (MRC), Chungbuk National University, Cheongju 362-763, KoreaA concise and expeditious approach to the total synthesis of broussonone A, a p-quinol natural compound, has been developed. The key features of the synthesis include the Grubbs II catalyst mediated cross metathesis of two aromatic subunits, and a chemoselective oxidative dearomatizationin the presence of two phenol moieties. Especially, optimization associated with the CM reaction of ortho-alkoxystyrenes was also studied, which are known to be ineffective for Ru-catalyzed metathesis reactions under conventional reaction conditions because ortho-alkoxy group could coordinate to the ruthenium center, resulting in the potential complication of catalyst inhibition.http://www.mdpi.com/1420-3049/20/9/15966broussonone Across metathesisGrubbs catalystoxidative dearomatizationPIFAtotal synthesis |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Hyeju Jo Minho Choi Mayavan Viji Young Hee Lee Young-Shin Kwak Kiho Lee Nam Song Choi Yeon-Ju Lee Heesoon Lee Jin Tae Hong Mi Kyeong Lee Jae-Kyung Jung |
| spellingShingle |
Hyeju Jo Minho Choi Mayavan Viji Young Hee Lee Young-Shin Kwak Kiho Lee Nam Song Choi Yeon-Ju Lee Heesoon Lee Jin Tae Hong Mi Kyeong Lee Jae-Kyung Jung Concise Synthesis of Broussonone A Molecules broussonone A cross metathesis Grubbs catalyst oxidative dearomatization PIFA total synthesis |
| author_facet |
Hyeju Jo Minho Choi Mayavan Viji Young Hee Lee Young-Shin Kwak Kiho Lee Nam Song Choi Yeon-Ju Lee Heesoon Lee Jin Tae Hong Mi Kyeong Lee Jae-Kyung Jung |
| author_sort |
Hyeju Jo |
| title |
Concise Synthesis of Broussonone A |
| title_short |
Concise Synthesis of Broussonone A |
| title_full |
Concise Synthesis of Broussonone A |
| title_fullStr |
Concise Synthesis of Broussonone A |
| title_full_unstemmed |
Concise Synthesis of Broussonone A |
| title_sort |
concise synthesis of broussonone a |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2015-09-01 |
| description |
A concise and expeditious approach to the total synthesis of broussonone A, a p-quinol natural compound, has been developed. The key features of the synthesis include the Grubbs II catalyst mediated cross metathesis of two aromatic subunits, and a chemoselective oxidative dearomatizationin the presence of two phenol moieties. Especially, optimization associated with the CM reaction of ortho-alkoxystyrenes was also studied, which are known to be ineffective for Ru-catalyzed metathesis reactions under conventional reaction conditions because ortho-alkoxy group could coordinate to the ruthenium center, resulting in the potential complication of catalyst inhibition. |
| topic |
broussonone A cross metathesis Grubbs catalyst oxidative dearomatization PIFA total synthesis |
| url |
http://www.mdpi.com/1420-3049/20/9/15966 |
| work_keys_str_mv |
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